US9056863B2ActiveUtilityPatentIndex 45
Substituted 2,3,5,9,9B-pentaazacyclopenta[a]naphthalenes and uses thereof
Est. expirySep 9, 2031(~5.2 yrs left)· nominal 20-yr term from priority
A61P 25/18A61P 25/28A61P 25/22C07D 471/14A61P 25/00
45
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Cited by
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References
23
Claims
Abstract
The present invention is directed to pyridine compounds of Formula (I). Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds as therapeutic agents treating neurological and psychiatric disorders.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A compound of Formula I:
wherein each X 1 , X 2 , and X 3 is independently CR 3 and X 4 is N;
wherein R 1 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, tetrahydropyranyl, benzyl, phenyl and pyridyl, in which the benzyl, phenyl and pyridyl is optionally substituted with one or more halogen, CN, C 1 -C 4 alkyl, C 1 -C 4 fluoroalkyl, C 1 -C 4 alkoxy, or C 1 -C 4 fluoroalkoxy;
wherein R 2 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl; and
wherein R 3 is hydrogen, halogen, CN, —CO 2 H, —CONH 2 , —CON(C 1 -C 4 alkyl) 2 , CHO, C 1 -C 4 alkyl, C 1 -C 4 fluoroalkyl, a cyclic amino containing heterocycle, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, or C 1 -C 4 fluoroalkoxy; or a pharmaceutically acceptable salt thereof.
2. The compound of claim 1 , wherein R 2 is C 1 -C 4 alkyl.
3. The compound of claim 1 or 2 , wherein R 2 is methyl.
4. The compound of claim 1 , wherein R 2 is C 3 -C 6 cycloalkyl.
5. The compound of claim 1 , wherein R 1 is C 1 -C 4 alkyl.
6. The compound of claim 1 , wherein R 1 is C 3 -C 6 cycloalkyl.
7. The compound of claim 1 , wherein R 1 is tetrahydropyranyl.
8. The compound of claim 1 , wherein R 1 is benzyl optionally substituted with one or two F, CI or C 1 -C 3 alkyl.
9. The compound of claim 1 , wherein R 1 is phenyl optionally substituted with one or two F, CI or C 1 -C 3 alkyl.
10. The compound of claim 1 , wherein R 1 is pyridyl optionally substituted with one or two F, CI or C 1 -C 3 alkyl.
11. The compound of claim 1 , wherein R 1 is phenyl substituted with one or two F, Cl or C 1 -C 3 alkyl.
12. The compound of claim 1 , wherein R 3 is hydrogen.
13. The compound of claim 1 , wherein R 3 is halogen or CHO.
14. The compound of claim 1 , wherein R 3 is C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
15. The compound of claim 1 , wherein R 3 is C 2 -C 4 alkenyl or C 2 -C 4 alkynyl.
16. The compound of claim 1 , wherein R 3 is a cyclic amino containing heterocycle.
17. The compound of claim 1 , wherein the compound is 1-(2-Chloro-phenyl)-4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene.
18. The compound of claim 1 , wherein the compound is 1-(2,6-Dichloro-phenyl)-4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene.
19. The compound of claim 1 , wherein the compound is 1-(2,6-Dimethyl-phenyl)-4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene.
20. The compound of claim 1 , wherein in the compound is 1-(2-Chloro-6-methyl-phenyl)-4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene.
21. The compound of claim 1 , wherein the compound is 1-(2-Chloro-phenyl)-6-methoxy-4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene.
22. The compound of claim 1 , wherein the compound is 1-(3-Chloro-phenyl)-4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalene.
23. A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.Cited by (0)
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